反应详情

A solution of 2-methyl-3-nitrobenzyl chloride (1.07 g) in dimethylformamide (30 ml) was added dropwise to a solution of di-t-butyl iminodicarboxylate (1.38 g) and sodium hydride (content, 60%; 0.30 g) in dimethylformamide (30 ml) at 0° C. Following 1-h stirring at room temperature, the temperature of the mixture was raised to 80° C. and stirred for 1 h. The reaction mixture was concentrated under reduced pressure, water was added to the residue, and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried with anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=10:1) to give 1.49 g of the titled compound (yield, 96%).

1. temperaturethe temperature of the mixture was raised to 80° C.
2. stirringstirred for 1 h
3. concentrationThe reaction mixture was concentrated under reduced pressure, water
4. additionwas added to the residue
5. extractionthe mixture was extracted with ethyl acetate
6. washThe organic layer was washed with a saturated aqueous sodium chloride solution
7. dry with materialdried with anhydrous sodium sulfate
8. concentrationconcentrated under reduced pressure
9. customThe resulting residue was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=10:1)